Chris Penn’s life and death can best be described as a cocktail. Booze, drugs, food: the little brother to one of his generation’s greatest actors, Sean Penn, was a walking blender. A close friend summed it up thus: “He’d think nothing of ordering five steaks, a couple of portions of fish and chips, followed by pints of chocolate milkshake and shots of 130 [proof] whisky. Chris lived on the edge and didn’t give a damn about the health risks. If it wasn’t food or drink he was having to excess it was cocaine.”

Most remember Chris Penn for his portrayal of Nice Guy Eddie in 1992’s Reservoir Dogs. But it was his performance as the ineffectual pool cleaner Jerry Kaiser in Robert Altman’s 1993 film Short Cuts that put the industry on notice. With his wife working from home as a phone-sex worker, Kaiser becomes increasingly angry, horny and insecure. A bad emotional mix resulting in some dark times for Kaiser and his phone-fellating wife.

A true American mutt, Penn’s ancestry included Jewish Lithuanian, Russian, Italian, Irish and a hint of Spanish stock. Another good cocktail. His actress mother, Eileen Ryan, appeared in Parenthood and Magnolia, among other films, while his father, Leo Penn, was a successful actor and director who was blacklisted in the 1950s for his communist tendencies and vocal support of Hollywood trade unions. Penn was 12 when he made his first screen appearance in Charlie and the Talking Buzzard. His classmates at Santa Monica High School included Charlie Sheen, Emilio Estevez and Rob Lowe – all of whom took acting classes with Penn at Peggy Feury’s Loft Studio. Penn was expelled from high school and took up boxing before landing roles in Francis Ford Coppola’s Rumble Fish in 1981 Footloose in 1984 and with Clint Eastwood in Pale Rider in 1985.

His knack for embodying his characters with his own sometimes troubled life proved irresistible to casting directors and audiences. He was the kind of palooka who could punch your lights out and you’d still buy him a drink. Either way there’d be drinking and fighting involved. He was once thrown out of a bar for fighting a midget. After insults and punches were traded, Penn was dragged out, screaming, “Let me at that midget!” His rap sheet included carrying an unlicensed gun.

Drinking and fighting were big in Penn’s repertoire and his acting was often underrated. Like best friend Michael Madsen, his party-boy existence often found him starring in solid gold turkeys. But he was rewarded for his screen work in 1996 when he won best supporting actor at the Venice Film Festival for his performance (and singing) in the gangster epic The Funeral.

Penn was the baby of the family. The oldest is musician Michael Penn, whom you may remember for his quasi-hit of 1989, No Myth. But it was middle child Sean who hogged the spotlight and the headlines with his own bad-boy ways, memorable screen performances and a very public marriage and divorce to Madonna. Many felt his celebrity status overshadowed what Chris offered as an actor. “He makes you seamlessly believe in characters so much you barely even notice them… Sean is a showboat, a scenery chewer; Chris is the opposite – a stealth bomb. Just as talented as Sean – just a lot less cocky,” Slate magazine critic Cinfra Wilson wrote.

Chris Penn, towards the end

Penn preferred to remain in the background where he could enjoy the good life (and how) without the prying eyes of the media and public. So successful was he about maintaining the mystery that when he was found in his Santa Monica condominium in January 2006, he’d been dead for three days (with a gun on the bedside table and one under the pillow, naturally). The cops said he was 40 but other sources claimed he was 43. Penn had been cagey about his age for years. Answering the question in a 1996 interview, he said, “I’m getting up there… I’ve stopped saying.”

This speculation was ended by the one person who could unequivocally say exactly how old he was – his mother, who confirmed he was go when a diet of steak, chocolate milkshakes, beer, prornethazine, codeine, marijuana and cocaine stopped his enlarged heart. Hell of a cocktail.